Chemistry:Homosildenafil

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Short description: Chemical compound
Homosildenafil
Homosildenafil.svg
Clinical data
ATC code
  • None
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC23H32N6O4S
Molar mass488.61 g·mol−1
3D model (JSmol)

Homosildenafil (also known as methyl-sildenafil) is a synthetic drug which acts as a phosphodiesterase inhibitor.[1] It is an analog of sildenafil and vardenafil. Homosildenafil was first identified as an adulterant in sex enhancement products in 2003 and was more recently detected in dietary supplements.[2][3][4][5]

Homosildenafil has 35% the PDE5 inhibition activity of sildenafil itself with similar selectivity.[1]

Sildenafil is mainly metabolized by the microsomal isozymes CYP3A4 with secondary metabolism by CYP2C9. The major active metabolite is N-desmethylsildenafil. The plasma level of the equivalent homosildenafil metabolite reaches 40% of sildenafil's bioavailability. The N-desmethyl metabolite is further metabolized, with a half-life of 4 hours.[6][7][8][9]

See also

References

  1. ↑ 1.0 1.1 "Vardenafil: structural basis for higher potency over sildenafil in inhibiting cGMP-specific phosphodiesterase-5 (PDE5)". Neurochemistry International 45 (6): 859–63. November 2004. doi:10.1016/j.neuint.2004.03.016. PMID 15312980. 
  2. ↑ "Identification of a new analogue of sildenafil added illegally to a functional food marketed for penile erectile dysfunction". Food Additives and Contaminants 20 (9): 793–6. September 2003. doi:10.1080/0265203031000121455. PMID 13129773. 
  3. ↑ "Detection of undeclared erectile dysfunction drugs and analogues in dietary supplements by ion mobility spectrometry". Journal of Pharmaceutical and Biomedical Analysis 49 (3): 601–6. April 2009. doi:10.1016/j.jpba.2008.12.002. PMID 19150190. 
  4. ↑ "Advisory - "Forta for Men" sex enhancement product recalled; contains undeclared drug". PR Newswire. 2014. http://www.prnewswire.com/news-releases/advisory---forta-for-men-sex-enhancement-product-recalled-contains-undeclared-drug-287148791.html. 
  5. ↑ "Simultaneous determination of synthetic phosphodiesterase-5 inhibitors found in a dietary supplement and pre-mixed bulk powders for dietary supplements using high-performance liquid chromatography with diode array detection and liquid chromatography-electrospray ionization tandem mass spectrometry". Journal of Chromatography A 1104 (1–2): 113–22. February 2006. doi:10.1016/j.chroma.2005.11.103. PMID 16364350. 
  6. ↑ De Tejada IS, Ferguson KM, Whitaker JS, "Daily treatment for erectile dysfunction using a pde5 inhibitor", WO patent 2001080860, published 1 November 2001, assigned to Lilly ICOS LLC.
  7. ↑ Borrello IM, Serafini P, Noonan KA, Bronte V, "Pde5 inhibitor compositions and methods for immunotherapy", US patent 20090074796, published 19 March 2009, assigned to ohns Hopkins University.
  8. ↑ Chen IJ, "Processes for preparing amine salts of sildenafil-analogues and use thereof", US patent 8497370, issued 30 July 2013, assigned to Kaohsiung Medical University.
  9. ↑ Yang X, Guo J, Huang Z, "Preparation method for monoclonal antibody specifically binding vardenafil and analog thereof", CN patent 101555512, issued 30 July 2013, assigned to Kaohsiung Medical University.

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